Acetic Anhydride → 19-Hydroxy-4-methyl-4-androstene3,17-dione acetate

HRID 1834947Notes

Reaction equation

HRID 1834947 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[C:7]([CH3:22])[C:6](=[O:23])[CH2:5][CH2:4]2.[C:24]([O:27]C(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([OH:27])(=[O:26])[CH3:25].[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[C:7]([CH3:22])[C:6](=[O:23])[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5379505019-Hydroxy-4-methyl-4-androstene-3,17-dione

Product 1

HCID 8673474619-Hydroxy-4-methyl-4-androstene3,17-dione acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

19-Hydroxy-4-methyl-4-androstene-3,17-dione is stirred under nitrogen with acetic anhydride and pyridine for about 16 hours. The yellow solution is poured onto water and the precipitate collected by suction filtration and washed well with water. Crystallization from acetone-hexane yield the desired 19-hydroxy-4-methyl-4-androstene3,17-dione acetate.

Workup

  1. additionThe yellow solution is poured onto water
  2. filtrationthe precipitate collected by suction filtration
  3. washwashed well with water
  4. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-640894a25c464c9e909d1e12d48aa2bd
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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